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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:40 UTC

Update Date

2022-03-07 02:52:28 UTC

HMDB ID

HMDB0030245

Secondary Accession Numbers

HMDB30245

Metabolite Identification

Common Name

Nornantenine

Description

Nornantenine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Nornantenine is a very strong basic compound (based on its pKa). Outside of the human body, nornantenine has been detected, but not quantified in, herbs and spices. This could make nornantenine a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0030245
     RDKit          3D
Nornantenine
 43 47  0  0  0  0  0  0  0  0999 V2000
   -3.4667    3.5171    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620    3.1056    0.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199    1.7775    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    0.7772    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848   -0.5379    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -0.7965    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773    0.1836   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4680    1.4728    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790    2.5602    0.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    3.1999   -1.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3253   -0.1513   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3029    0.8160   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145    0.4222   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478   -0.9122   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -1.8642   -0.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493   -1.4911   -0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6620   -2.5658   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7349   -2.2226   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -2.9017    1.1009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7508   -2.9454    0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3767   -1.6281    0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3286   -1.0335   -0.8090 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9130    0.2151   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8303    1.1101   -0.6321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184    2.9648    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5720    4.5904    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7151    3.3506    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7749    1.0176    0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    3.4370   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9388    4.1188   -1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7107    2.5042   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418    1.8311   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093   -2.9060   -0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516   -3.1438   -1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162   -3.3145    0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -2.5806   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0391   -2.4838    1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2188   -3.4068    1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086   -3.6317    0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353   -1.7090   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545   -1.3513    1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7689    0.4458   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1612    0.1602    0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 14 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 16 11  1  0
 21  5  1  0
 18  6  1  0
 24 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
M  END


  Mrv0541 05061305062D          

 24 28  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2708   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7859   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16  6  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  2  0  0  0  0
 19 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20  4  1  0  0  0  0
 20 13  1  0  0  0  0
 21  1  1  0  0  0  0
 21 16  1  0  0  0  0
 22  2  1  0  0  0  0
 22 19  1  0  0  0  0
 23  9  1  0  0  0  0
 23 14  1  0  0  0  0
 24  9  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030245

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C3C(CC4=CC5=C(OCO5)C=C24)NCCC3=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO4/c1-21-16-6-10-3-4-20-13-5-11-7-14-15(24-9-23-14)8-12(11)18(17(10)13)19(16)22-2/h6-8,13,20H,3-5,9H2,1-2H3

> <INCHI_KEY>
JWXKBCGJLCEZTJ-UHFFFAOYSA-N

> <FORMULA>
C19H19NO4

> <MOLECULAR_WEIGHT>
325.3585

> <EXACT_MASS>
325.131408101

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.163557158754955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(20),2,4(8),9,16,18-hexaene

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.626255026666666

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.452367730870954

> <JCHEM_POLAR_SURFACE_AREA>
48.95

> <JCHEM_REFRACTIVITY>
89.42489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(20),2,4(8),9,16,18-hexaene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030245
     RDKit          3D
Nornantenine
 43 47  0  0  0  0  0  0  0  0999 V2000
   -3.4667    3.5171    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620    3.1056    0.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199    1.7775    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    0.7772    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848   -0.5379    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -0.7965    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773    0.1836   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4680    1.4728    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790    2.5602    0.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    3.1999   -1.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3253   -0.1513   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3029    0.8160   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145    0.4222   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478   -0.9122   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -1.8642   -0.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493   -1.4911   -0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6620   -2.5658   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7349   -2.2226   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -2.9017    1.1009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7508   -2.9454    0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3767   -1.6281    0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3286   -1.0335   -0.8090 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9130    0.2151   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8303    1.1101   -0.6321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184    2.9648    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5720    4.5904    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7151    3.3506    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7749    1.0176    0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    3.4370   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9388    4.1188   -1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7107    2.5042   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418    1.8311   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093   -2.9060   -0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516   -3.1438   -1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162   -3.3145    0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -2.5806   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0391   -2.4838    1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2188   -3.4068    1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086   -3.6317    0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353   -1.7090   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545   -1.3513    1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7689    0.4458   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1612    0.1602    0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 14 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 16 11  1  0
 21  5  1  0
 18  6  1  0
 24 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.705  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.800  -2.786   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.800  -0.294   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4   10                                                       
CONECT    4    3   20                                                       
CONECT    5   11   13                                                       
CONECT    6   10   16                                                       
CONECT    7   11   14                                                       
CONECT    8   12   15                                                       
CONECT    9   23   24                                                       
CONECT   10    3    6   17                                                  
CONECT   11    5    7   12                                                  
CONECT   12    8   11   18                                                  
CONECT   13    5   17   20                                                  
CONECT   14    7   15   23                                                  
CONECT   15    8   14   24                                                  
CONECT   16    6   19   21                                                  
CONECT   17   10   13   18                                                  
CONECT   18   12   17   19                                                  
CONECT   19   16   18   22                                                  
CONECT   20    4   13                                                       
CONECT   21    1   16                                                       
CONECT   22    2   19                                                       
CONECT   23    9   14                                                       
CONECT   24    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0030245
HETATM    1  C1  UNL     1      -3.467   3.517   0.892  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.162   3.106   0.594  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.820   1.777   0.442  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.739   0.777   0.576  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.385  -0.538   0.422  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.048  -0.796   0.128  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.077   0.184  -0.013  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.468   1.473   0.140  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.379   2.560   0.012  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.323   3.200  -1.304  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.325  -0.151  -0.269  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.303   0.816  -0.336  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.614   0.422  -0.519  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.948  -0.912  -0.632  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.972  -1.864  -0.562  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.649  -1.491  -0.380  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.662  -2.566  -0.305  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.735  -2.223  -0.056  1.00  0.00           C  
HETATM   19  N1  UNL     1      -1.318  -2.902   1.101  1.00  0.00           N  
HETATM   20  C17 UNL     1      -2.751  -2.945   0.895  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.377  -1.628   0.569  1.00  0.00           C  
HETATM   22  O3  UNL     1       5.329  -1.033  -0.809  1.00  0.00           O  
HETATM   23  C19 UNL     1       5.913   0.215  -0.479  1.00  0.00           C  
HETATM   24  O4  UNL     1       4.830   1.110  -0.632  1.00  0.00           O  
HETATM   25  H1  UNL     1      -4.218   2.965   0.308  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.572   4.590   0.618  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.715   3.351   1.973  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.775   1.018   0.809  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.714   3.437  -1.570  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.939   4.119  -1.302  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.711   2.504  -2.075  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.142   1.831  -0.217  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.209  -2.906  -0.647  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.752  -3.144  -1.285  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.016  -3.314   0.455  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.349  -2.581  -0.924  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.039  -2.484   1.995  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.219  -3.407   1.787  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.909  -3.632   0.016  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.035  -1.709  -0.323  1.00  0.00           H  
HETATM   41  H17 UNL     1      -4.055  -1.351   1.412  1.00  0.00           H  
HETATM   42  H18 UNL     1       6.769   0.446  -1.116  1.00  0.00           H  
HETATM   43  H19 UNL     1       6.161   0.160   0.609  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   28
CONECT    5    6    6   21
CONECT    6    7   18
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10
CONECT   10   29   30   31
CONECT   11   12   12   16
CONECT   12   13   32
CONECT   13   14   14   24
CONECT   14   15   22
CONECT   15   16   16   33
CONECT   16   17
CONECT   17   18   34   35
CONECT   18   19   36
CONECT   19   20   37
CONECT   20   21   38   39
CONECT   21   40   41
CONECT   22   23
CONECT   23   24   42   43
END

HMDB0030245
     RDKit          3D
Nornantenine
 43 47  0  0  0  0  0  0  0  0999 V2000
   -3.4667    3.5171    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620    3.1056    0.5935 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199    1.7775    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7395    0.7772    0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3848   -0.5379    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0479   -0.7965    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773    0.1836   -0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4680    1.4728    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790    2.5602    0.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3231    3.1999   -1.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3253   -0.1513   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3029    0.8160   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145    0.4222   -0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478   -0.9122   -0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -1.8642   -0.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6493   -1.4911   -0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6620   -2.5658   -0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7349   -2.2226   -0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3179   -2.9017    1.1009 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7508   -2.9454    0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3767   -1.6281    0.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3286   -1.0335   -0.8090 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9130    0.2151   -0.4795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8303    1.1101   -0.6321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2184    2.9648    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5720    4.5904    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7151    3.3506    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7749    1.0176    0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    3.4370   -1.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9388    4.1188   -1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7107    2.5042   -2.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418    1.8311   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2093   -2.9060   -0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7516   -3.1438   -1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162   -3.3145    0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489   -2.5806   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0391   -2.4838    1.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2188   -3.4068    1.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086   -3.6317    0.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353   -1.7090   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0545   -1.3513    1.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7689    0.4458   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1612    0.1602    0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 14 22  1  0
 22 23  1  0
 23 24  1  0
  8  3  1  0
 16 11  1  0
 21  5  1  0
 18  6  1  0
 24 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 15 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
 23 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Nornantenine	HMDB
1,2-Dimethoxy-9,10-methylenedioxynoraporphine	HMDB
N-Nornantenine	HMDB

Chemical Formula

C₁₉H₁₉NO₄

Average Molecular Weight

325.3585

Monoisotopic Molecular Weight

325.131408101

IUPAC Name

18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(20),2,4(8),9,16,18-hexaene

Traditional Name

18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(20),2,4(8),9,16,18-hexaene

CAS Registry Number

15401-66-8

SMILES

COC1=C(OC)C2=C3C(CC4=CC5=C(OCO5)C=C24)NCCC3=C1

InChI Identifier

InChI=1S/C19H19NO4/c1-21-16-6-10-3-4-20-13-5-11-7-14-15(24-9-23-14)8-12(11)18(17(10)13)19(16)22-2/h6-8,13,20H,3-5,9H2,1-2H3

InChI Key

JWXKBCGJLCEZTJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Organoheterocyclic compound
Azacycle
Secondary amine
Oxacycle
Acetal
Ether
Secondary aliphatic amine
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030245)
Cytoplasm (HMDB: HMDB0030245)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030245)

Source

Endogenous

Endogenous (HMDB: HMDB0030245)

Plant

Plant (HMDB: HMDB0030245)

Exogenous

Food

Food (HMDB: HMDB0030245)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	163 - 164 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.035 g/L	ALOGPS
logP	1.82	ALOGPS
logP	2.63	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	9.45	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	48.95 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.42 m³·mol⁻¹	ChemAxon
Polarizability	35.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.571	31661259
DarkChem	[M-H]-	175.36	31661259
DeepCCS	[M-2H]-	219.171	30932474
DeepCCS	[M+Na]+	194.399	30932474
AllCCS	[M+H]+	176.7	32859911
AllCCS	[M+H-H2O]+	173.4	32859911
AllCCS	[M+NH4]+	179.7	32859911
AllCCS	[M+Na]+	180.6	32859911
AllCCS	[M-H]-	183.8	32859911
AllCCS	[M+Na-2H]-	183.1	32859911
AllCCS	[M+HCOO]-	182.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nornantenine	COC1=C(OC)C2=C3C(CC4=CC5=C(OCO5)C=C24)NCCC3=C1	4163.8	Standard polar	33892256
Nornantenine	COC1=C(OC)C2=C3C(CC4=CC5=C(OCO5)C=C24)NCCC3=C1	2710.0	Standard non polar	33892256
Nornantenine	COC1=C(OC)C2=C3C(CC4=CC5=C(OCO5)C=C24)NCCC3=C1	2969.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nornantenine,1TMS,isomer #1	COC1=CC2=C3C(=C1OC)C1=CC4=C(C=C1CC3N([Si](C)(C)C)CC2)OCO4	2855.4	Semi standard non polar	33892256
Nornantenine,1TMS,isomer #1	COC1=CC2=C3C(=C1OC)C1=CC4=C(C=C1CC3N([Si](C)(C)C)CC2)OCO4	2885.8	Standard non polar	33892256
Nornantenine,1TBDMS,isomer #1	COC1=CC2=C3C(=C1OC)C1=CC4=C(C=C1CC3N([Si](C)(C)C(C)(C)C)CC2)OCO4	3076.2	Semi standard non polar	33892256
Nornantenine,1TBDMS,isomer #1	COC1=CC2=C3C(=C1OC)C1=CC4=C(C=C1CC3N([Si](C)(C)C(C)(C)C)CC2)OCO4	3107.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nornantenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-01oy-0092000000-f636e648a179ec3f5c26	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nornantenine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 10V, Positive-QTOF	splash10-004i-0019000000-472771b99e21598ebaa4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 20V, Positive-QTOF	splash10-004i-0049000000-0e2b5ef04470fe2343b6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 40V, Positive-QTOF	splash10-01oy-0290000000-5186d25c733dac245d78	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 10V, Negative-QTOF	splash10-00di-0009000000-eb1eb37eda7f1664ee7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 20V, Negative-QTOF	splash10-00di-0039000000-dcda59b6a47ac3e39039	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 40V, Negative-QTOF	splash10-0570-1091000000-c1da2bebd5c387d34083	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 10V, Positive-QTOF	splash10-004i-0009000000-8258216b4e41e9caadf2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 20V, Positive-QTOF	splash10-004i-0009000000-8f9a2e8dd259c02197b1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 40V, Positive-QTOF	splash10-007k-0092000000-830864c38a043f1ae8a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 10V, Negative-QTOF	splash10-00di-0009000000-fd8a579508e412fbe114	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 20V, Negative-QTOF	splash10-00di-0019000000-3a97888dbd6a22677a4a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nornantenine 40V, Negative-QTOF	splash10-00xu-0094000000-024a38dd0ca859e583d1	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002068

KNApSAcK ID

C00025269

Chemspider ID

2341325

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3084228

PDB ID

Not Available

ChEBI ID

804420

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Nornantenine (HMDB0030245)

MOL for HMDB0030245 (Nornantenine)

3D MOL for HMDB0030245 (Nornantenine)

3D SDF for HMDB0030245 (Nornantenine)

3D-SDF for HMDB0030245 (Nornantenine)

PDB for HMDB0030245 (Nornantenine)

3D PDB for HMDB0030245 (Nornantenine)

SMILES for HMDB0030245 (Nornantenine)

INCHI for HMDB0030245 (Nornantenine)

Structure for HMDB0030245 (Nornantenine)

3D Structure for HMDB0030245 (Nornantenine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra